This website or its third-party tools use cookies which are necessary to its functioning and required to improve your experience. By clicking the consent button, you agree to allow the site to use, collect and/or store cookies.

What is “Strategic Freelancing” Anyway?

I’m a big believer that most of our freelance “failures” eventually point back to not being able to state why we’re freelancing in the first place, and then not having a plan that’s grounded in that ‘why’.

If you follow me over on Twitter you’ve probably seen me mention “Strategic Freelancing”. It’s a concept I credit for my own freelance career and what everything here at BlackFreelance points back to.

A strategic approach to this freelancing is why I offer everybody here a copy of the BlackFreelace Strategy Workbook as soon as you set foot in the door — I want everyone who comes by this platform to find a way to use freelancing to improve their life — and I want you to get there faster and skip over the frustration that has so many people missing out on the benefits freelancing offers.

All that? Starts with strategy.

Strategy matters in this game and it can make the difference between a freelance career that benefits your life and one that leaves you running back to over-reliance on employment, so let’s talk about it a little.

Strategic Freelancing is Proactive Freelancing.

Strategic Freelancing is what keeps you out of a LOT of the trouble that has other freelancers frustrated and caught up in low-paying, exploitative work for years on top of decades. It should be in your head if you’re even thinking about kind of considering, maybe, possibly trying out freelancing.

Don’t wait and have to course correct months or even years down the road. Get it right from the jump.

Strategic Freelancing is Informed Freelancing.

There’s just no good argument for doing this work outside of the realities of business.

We’re subject to the same market forces, labor trends, and business rules as everybody else, and we have just as much reason as any job seeker or entrepreneur to base our freelance decisions on solid information and business realities.

Strategic Freelancing doesn’t ask “What am I good at?”. It looks for alignment between what it can do and what’s in demand.

Strategic Freelancing knows that passion is overrated and the highest-visibility freelance work (things like writing for digital media) also tend to be the lowest paying, most exploitative, and fastest dying. There’s a better way and looking for good information will help you find it.

Strategic Freelancing is Personal.

There’s a lot of typical business stuff I don’t care about. That includes startup hype, “entrepreneur” status, busy-ness as a culture, and the inherent value of hustle.

…but that’s me. You might feel differently about all those things, and that’s ok!

I don’t care if you just want to make an extra $500 a month to supplement your full-time income, have freedom from employer repercussions for your work as an activist, or reach the ranks of a 7-figure freelancer and turn that into your own startup — your freelance business should work for you. It should enhance your life, not be in the driver’s seat.

You can get any job to run your life with the perk of a steady paycheck and easier retirement, so why settle for the same results just for more effort and less stability?

The BlackFreelance Workbook starts off asking you what you want freelancing to do for your life for a reason. If you don’t start with (and regularly revisit) that question, you can end up with a business, and a life, that you never wanted in the first place.

The happiest and most successful freelancers develop and practice discipline in our work, and that discipline works best when it’s connected to a deliberate strategy.

Strategic Freelancing is Leveraged Freelancing.

One of the worst mistakes a new freelancer can make is trying to reinvent the wheel by jumping into an entirely new field.

I get why some of us want to do that.

When I started freelancing, I wanted NATHAN to do with my old job. It took me two years before I could take a client in my field without feeling sick to my stomach. But before that, I still made sure I leveraged my education and the parts of my career experience that hadn’t left me scarred.

Freelancing and employment are very closely related. That means both can and should feed off and inform each other across a career. Anything less is probably wasted opportunity.

Strategic Freelancing is Responsible.

Freelancing by definition means that you’re taking responsibility for a lot of the things employers used to do for you. Stuff like

It takes a while to get a feel for all those things, but anything less than that is dancing in the space between employment and freelancing, and that’s where the most exploitation happens. A strong strategy can help you steer clear.

Strategic Freelancing is Prepared Freelancing.

I tell people who are interested in full-time freelancing that asking “When can I quit my job?” is the wrong question to start with.

Strategic freelancing acknowledges that it takes time to find your groove (people say 2 years) and time to feel comfortable (people say 9 years) in this business.

Unlike me (who waited until after a layoff and health issues forced me to choose) prepared freelancers start before they need to. They prioritize earning and savings, and acknowledge challenges like high tax rates (30-40%), legal protections, and skill development, right off the bat.

Strategic Freelancing Happens in Community.

Strategy doesn’t start in a vacuum — at least it shouldn’t.

Freelancing means you’re running a business separate from the constant feedback and connection you get from employment. Freelancers have to make up for this disconnect by deliberately engaging with people in the same field, the same skill set, and in general freelance communities.